Trifluoromethanesulfonic anhydride → 6-[1-Hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthyl Trifluoromethanesulfonate

HRID 480445노트

반응식

HRID 480445 반응식
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[OH:16][C:17]([C:45]1[CH:46]=[C:47]2[C:52](=[CH:53][CH:54]=1)[CH:51]=[C:50](O)[CH:49]=[CH:48]2)([C:21]1[N:22]=[CH:23][N:24]([C:26]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=1)[CH:18]([CH3:20])[CH3:19]>N1C=CC=CC=1.O>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:50]1[CH:49]=[CH:48][C:47]2[C:52](=[CH:53][CH:54]=[C:45]([C:17]([OH:16])([C:21]3[N:22]=[CH:23][N:24]([C:26]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:25]=3)[CH:18]([CH3:19])[CH3:20])[CH:46]=2)[CH:51]=1)(=[O:5])=[O:4]

참가 물질

5

반응물 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 220183856-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthol

생성물 1

HCID 222850556-[1-Hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthyl Trifluoromethanesulfonate

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매

반응 조건

온도
0 °C

실험 절차

Trifluoromethanesulfonic anhydride (9.1 mL) was added dropwise to a solution of 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthol (27.0 g) in pyridine (200 mL) at 0° C. The reaction mixture was stirred for 1 h at 0° C., diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated. The residue was purified by silica gel column chromatography (eluent; hexane-ethyl acetate=1:1). Crystallization from diisopropyl ether gave the titled compound (29.6 g) as a colorless powder.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluent; hexane-ethyl acetate=1:1)
  6. customCrystallization from diisopropyl ether

출처 및 근거

ORD 기록
ord-572bb105840e4666833adeae9b41221f
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649643B1

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